The first charters will start around 1st November. If your friend wants to go in early October then it will have to be a scheduled flight via Mumbai or Sri Lanka.

Don't know about the weather as I have never been this early but the monsoon finished late last year and they were still having storms in October. I think the weather will be as predictable as expecting August in the UK to be warm and sunny.

every year we have gone charter around the 18th October usually with jewel in the crown and the dreaded monarch but have been looking and nothing seems to be coming up until 1st November